For Straight-from-SoHo Fashion
Crowds huddled in Ossing­ton’s doorways are a familiar sight, but nothing compares to the sidewalk jams that form when Jonathan and Olivia owner Jackie O’Brien holds her biannual sales (starting on Boxing Day and again in June or July). Cool kids, designers, ad execs and artsy-leaning scions flock here for deconstructed hipster wear from Manhattan, Sweden and the U.K., by the likes of Alexander Wang, Rag and Bone, Band of Outsiders, Engineered Garments, and Wings and Horns. All up to 50 per cent off. E-mail info@jonathanandolivia.com to get on the list.

FOR Big European Labels
Toronto retail veteran Elsa Reia was hosting sample sales long before they were in vogue, which explains her all-star roster of designer brands: apparel, accessories and footwear from Alexander McQueen, Rick Owens, Dries Van Noten, Miu Miu, Martin Margiela, Lanvin, Isabel Marant and more. The blowout runs over two days in April and October. Expect a variety of sizes and inventory, from recent and past seasons, marked down by 70 per cent or more. E-mail info@reiastudio.com to sign up.FOR High-End Jeans
Ideal for anyone who goes into sticker shock at the price of designer denim, the Sixty Canada sale features a mixed bag of it brands: Miss Sixty, Acne, Filippa K, Energie, Killah and Nudie Jeans, all 50 per cent off retail prices. Held twice yearly at the end of April and in October, the two-day event also includes clothing, footwear and accessories, plus some one-of-a-kind pieces not found in stores. Includes kids’ sizes 2 to 6. E-mail “Toronto sample sale” to info@sixtycanada.com.

FOR Designer Sporty Stuff
The Web outfit Style Democracy organizes and aggregates promotions as often as four times a week. Sign up and receive e-mails for a range of weekend sales across the city. Great for loads of active wear—generally at 50 to 80 per cent off—from a select group of household names, including Puma, Lacoste, Esprit, Fred Perry, Converse and Sporting Life. One constant: an endless sea of merch, sometimes up to 50,000 pieces per sale. Get on the list at styledemocracy.com.

FOR Kids’ Shoes
Every spring, and in late October or so, a mysterious outfit called Keno Sales draws hordes of BMW-driving parents to a low-rent Etobicoke plaza to stock up on several seasons’ worth of kiddie footwear by Geox, the Italian brand famous for its breathable Respira line. The deals are incredible: from $30 for ultra-durable and chic Euro schoolkid leather shoes and booties, compared to about $90 retail. No strollers, no food, no drink and no whining are allowed. There’s a kill or be killed mentality at play here, so elbow your way aggressively. Lots of $60 Geox loafers for men and women, too. Shoppers get on the e-mail list only by going to the sale itself. Scan redflagdeals.com starting in late March for details on the next one.

FOR Inspired Local Design
Only a Jeremy Laing end-of-season sale could draw the city’s most fashionable people to a hard-to-find studio on Queen near Jameson—not to mention get them to strip in a communal change room. For one day only, in the spring and before the fall (the last one was at the end of August), the boy-wonder designer’s thoughtful and multi-layered ensembles (alas, mostly in sizes 2 and 4) are priced at less than $400—a steal considering they run up to $1,000 retail. No list, and the sale is under-publicized. Doggedly bug the Jeremy Laing studio at 416-530-1976.